EP3887419A1 - Formulation de mousse de polyuréthane et isolations acoustiques comportant des mousses à base de cette formulation - Google Patents

Formulation de mousse de polyuréthane et isolations acoustiques comportant des mousses à base de cette formulation

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Publication number
EP3887419A1
EP3887419A1 EP19804674.0A EP19804674A EP3887419A1 EP 3887419 A1 EP3887419 A1 EP 3887419A1 EP 19804674 A EP19804674 A EP 19804674A EP 3887419 A1 EP3887419 A1 EP 3887419A1
Authority
EP
European Patent Office
Prior art keywords
component
formulation according
polyol
viscoelastic
foam
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP19804674.0A
Other languages
German (de)
English (en)
Inventor
Helmut Becker
Volkmar Schulze
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Adler Pelzer Holding GmbH
Original Assignee
Adler Pelzer Holding GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Adler Pelzer Holding GmbH filed Critical Adler Pelzer Holding GmbH
Publication of EP3887419A1 publication Critical patent/EP3887419A1/fr
Pending legal-status Critical Current

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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
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    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
    • C08G18/2027—Heterocyclic amines; Salts thereof containing one heterocyclic ring having two nitrogen atoms in the ring
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    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/285—Nitrogen containing compounds
    • C08G18/2865—Compounds having only one primary or secondary amino group; Ammonia
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    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
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    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
    • C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
    • C08G18/4222—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic polyhydroxy compounds and polycarboxylic acids
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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    • C08G18/48—Polyethers
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/485—Polyethers containing oxyethylene units and other oxyalkylene units containing mixed oxyethylene-oxypropylene or oxyethylene-higher oxyalkylene end groups
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    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
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    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
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    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
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    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
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    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
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    • C08G2110/00—Foam properties
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    • C08G2350/00—Acoustic or vibration damping material
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    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
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    • C08J2375/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
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    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C08J2375/08—Polyurethanes from polyethers

Definitions

  • the invention relates to a polyurethane foam formulation based on conventional polyether and polyester polyols (hybrid formulation) based on renewable raw materials with MDI for the production of preferably viscoelastic polyurethane (PUR) - molded foams and sound insulation with foams based thereon.
  • PUR viscoelastic polyurethane
  • Soft elastic and viscoelastic molded polyurethane foams are widely used in the field of vehicle acoustics.
  • Usual soft-elastic foams are generally assigned to the "high resilience” - that is, highly elastic type and have a distinctive spring characteristic with spontaneous or quick resilience. This is opposed by the visco-elastic foam types, which distinguish themselves from soft-elastic foam types by a differentiation characterized by delayed recovery behavior after compression deformation. Viscoelastic foams generally achieve much better damping properties than "high resilience" foams.
  • acoustically effective components in the field of vehicle acoustics are preferably produced directly as molded parts with the desired component geometry.
  • Two-component systems are generally used for this, one component of the reactive system being diverse (poly) isocyanates, the second component consisting of a complex mixture of mostly different polyols, blowing agents, catalysts, stabilizers and any other additives.
  • the typical material properties of these foams are primarily determined by the types of polyol used, their quantity distribution, the degree of crosslinking and the density selected. In view of the intended use, but also taking into account frequent intolerance, either polyester or polyether polyols are used. In the field of sound insulation, foams based on polyether polyols and MDI predominate.
  • the respective polyols differ essentially in terms of functionality, reactivity and molecular mass, the functionality and the basic structure being determined directly by the starter molecule used.
  • Water is usually added to the polyol component as a chemical blowing agent, the water reacting with the (poly) isocyanate and releasing carbon dioxide, which acts as an actual blowing agent.
  • Soft elastic foams are used in different versions for equally different acoustic applications.
  • the applications range from pure absorbers to spring-mass structures.
  • the insulation effect increases depending on the density or the combined mass layer.
  • viscoelastic molded foams are usually characterized by better damping properties and are therefore used particularly in the premium sector.
  • This viscoelastic material behavior can be divided into pneumatic effects and structural properties, but usually represents a combination of the two
  • pneumatic (“asthma”) effect is based on a very small pore size, often also in combination with an incompletely open cell structure, which slows down the exchange of air during compression and during recovery.
  • the structural properties result from the combination of soft and hard segments within the polymer matrix and can be controlled accordingly via the quantity distribution of differently functional polyols and the named primary parameters.
  • the corresponding modulus of elasticity plays a decisive role. In this way, comparatively harder foams, despite the high loss factor, can have worse acoustic insulation properties. hold than those with a low loss factor, but much lower hardness.
  • the efficiency of foamed, acoustically effective automotive trim parts is determined by the respective component concept as a whole, in particular by the special properties of the foam systems used.
  • the acoustic effectiveness is basically divided into the two categories absorption and insulation.
  • the degree of absorption of a molded foam component is primarily dependent on the porosity and size of the surface open to the sound and the internal cell morphology (cell size and distribution, number and ratio of open and closed cells), which on the other hand the performance-determining properties of flow resistance and tortuosity are essential influence.
  • the insulation properties of molded foams are determined by their density and the elastic spring properties.
  • the elasticity behavior plays a decisive role.
  • Both spring elastic and viscoelastic foam types are known, with viscoelastic versions in particular in a soft setting due to the higher insulation - expressed as a loss factor. tor - achieve significantly better insulation than spring-elastic foams in a comparable setting with regard to hardness and foamed density.
  • corresponding mass layers are generally used analogously to highly elastic foams and combined and so-called spring-mass elements and back-foamed.
  • the acoustic effectiveness of the overall structure is then further determined by the above-mentioned properties of the spring (molded foam), but additionally by the properties of the mass layer (basis weight, bending softness).
  • a higher weight per unit area with the same back-foaming generally leads to an improved damping of vibrating elements, which are mostly sheet metal in the automotive sector.
  • the sheets themselves are often constructively calmed and additionally equipped with (heavy) damping foils in order to improve the acoustic behavior.
  • this measure leads directly to a higher vehicle weight.
  • hydroxyl or OH number which is a measure of the content of hyd roxyl groups, and is given in mg KOH / g. It is determined in accordance with DIN 53240;
  • the polyols used differ in the starter molecule used, the resulting functionality, the molecular mass and the reactivity.
  • targeted modifications of the material behavior via the isocyanate component are possible, e.g. using prepolymers.
  • the aim of the present invention is to reverse the negative dependence of the loss factor and degree of crosslinking in terms of the desired acoustic effectiveness by using more suitable components, and in particular to significantly increase the loss factor of the molded foams produced in this way.
  • the significantly improved insulation effect of these molded foams thus represents the functional basis for sound insulation made from them.
  • a flybrid formulation is used in the present invention, in which conventional, petroleum-based polyether polyols, optionally with polyester diols based on renewable raw materials, here CNSL (Cashew Nut Shell Liquid) can be combined and significantly better acoustically effective material properties can be derived from this.
  • the special structure of the CNSL-based polyester diols in particular the characteristic, natural presence of hard segments in the form of an aromatic ring directly accessible via a hydroxyl group, but also the comparatively high reactivity of these polyester polyols means that even at low MDI index, a significantly higher loss factor in combination with a comparatively low modulus of elasticity can be achieved.
  • the same overall system coordination - i.e. the same MDI index and the same molded foam density - this leads to significantly improved acoustic material properties than when using conventional pure systems.
  • the starting material is based on renewable raw materials, which, in contrast to many other products based on vegetable oils, do not compete with food procurement, but as natural by-product can be obtained.
  • the formulations according to the invention are based on polyether polyols. Mixing with the CNSL-based polyester polyol leads to said flybrid formulations. In the field of use of acoustic components for the automotive sector, sort-of-type formulations, that is to say either polyether or polyester compositions, are customary, which have typical advantages and disadvantages depending on the intended use.
  • the polyester polyol used to prepare the hybrid formulations is preferably a polyester diol derived from CNSL (Cashew Nutshell Liquid).
  • Type designation Cardolite® NX-9203 (product of Cardolite Corporation), difunctional, with a hydroxyl number 98mgKOH / g, viscosity of 2650cps at 25 ° C and a calculated content of renewable raw materials of 69%.
  • the polyether polyols b), c) and d) according to the invention are preferably by polymerization of epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin with themselves or by addition of these epoxides, optionally in a mixture or in succession, to starting components with reactive Hydrogen atoms such as water, alcohols, ammonia or amines are produced here.
  • epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin
  • reactive Hydrogen atoms such as water, alcohols, ammonia or amines are produced here.
  • ethylene oxide and propylene oxide are particularly preferred.
  • the polyether polyols used are very particularly preferably built up only from propylene oxide as the epoxy component.
  • the latter can have any desired arrangement of the oxyalkylene units. Accordingly, it can be homopolymers (when only one epoxide is used), copolymers d), “random” copolymers, “capped” polymers or polymers that are tipped with a mixture of different epoxides to achieve a desired content of primary hydroxyl groups.
  • Renewable raw materials in the sense of the present invention are understood to mean compounds which occur in nature and can also be isolated in this form.
  • not being derived from a renewable raw material means that the carbon skeleton of the relevant renewable raw material is no longer contained within the polyether polyol of component (b). This means in particular that said polyether polyol is not obtained, for example, by reacting a renewable raw material with epoxides to form a polyether polyol.
  • Examples of possible renewable raw materials are castor oil, polyhydroxyfatty acid, castoriolic acid, oils modified with hydroxyl groups, such as grape seed oil, black cumin oil, pumpkin seed oil, borage seed oil, soybean oil, wheat germ oil, rapeseed oil, sunflower oil, peanut oil, apricot oil, avian oil, macadamia oil, macadamia oil, pistachio oil, pistachio oil, pistachio oil Sea buckthorn oil, sesame oil, hemp oil, hazelnut oil, evening primrose oil, wild rose oil, safflower oil, walnut oil, fatty acids modified with hydroxyl groups and fatty acid esters based on myristoleic acid, palmitoleic acid, oleic acid, vaccenic acid, pertoselic acid, gadoleic acid, erucic acid, nervonic acid, stearic acid, linoleic acid, and Arachidonic acid, timnodonic acid, clu
  • the above-mentioned renewable raw materials also include chemically modified compounds, in which, however, the connectivity of the carbon structure itself remains unchanged (for example, renewable raw materials modified with hydroxyl groups, formed, for example, by hydroxylation of compounds or hydrogenated products).
  • Possible starter compounds are, for example, dicarboxylic acids, such as succinic acid, adipic acid, phthalic acid and terephthalic acid.
  • starter compounds that can be used are, for example, ammonia or aliphatic and / or aromatic amines, which may be substituted, such as N-monoalkyl-, N, N-dialkyl- and / or N, N'-dialkyl-substituted diamines will. They have at least one primary or secondary amino group, such as, for example, 1,2-diaminoethane, oligomers of 1,2-diaminoethane (for example diethylenetriamine, triethylenetetramine or pentaethylene-hexamine), 1,3-diaminopropane, 1,3-diaminobutane, 1, 4-diaminobutane,
  • 1,2-diaminoethane oligomers of 1,2-diaminoethane (for example diethylenetriamine, triethylenetetramine or pentaethylene-hexamine), 1,3-diaminopropane, 1,3-diaminobutane, 1,
  • alkanolamines such as ethanolamine, N-methyl- and N-ethylethanolamine
  • dialkanolamines such as diethanolamine, N-methyl- and N-ethyldiethanolamine
  • trialkanolamines such as triethanolamine
  • Suitable starter compounds are those with two or more hydroxyl groups, such as water, 1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, diethylene glycol, dipropylene glycol, triethyl englycol, tripropylene glycol, 1,2-butanediol, 1 , 3-butanediol, 1,4-butanediol,
  • the starter compounds can be used alone or as mixtures.
  • the mass fractions of components (a) to (d) are preferably in the following amounts: (a) 10 to 45% by weight, particularly preferably 20 to 30% by weight; (b) 0 to 55% by weight, particularly preferably 5 to 20% by weight; (c) 40 to 75% by weight, particularly preferably 50 to 70% by weight and (d) 5 to 50% by weight, particularly preferably 5 to 20% by weight.
  • the data in% by weight relate to the total mass of the polypolyol composition. These proportions by weight are preferred in that they result in a particularly high viscoelasticity in the polyurethane foam according to the invention.
  • a triol is particularly preferably used as the starter molecule, in particular glycerol.
  • a 1,2-diol is preferably used as the starter molecule, in particular propylene glycol.
  • An acoustically effective motor capsule for electric motors is known, for example in the case of Tesla, Model S, structure of PUR soft foam and heavy film.
  • a high weight per unit area of the heavy film is necessary to present the required effectiveness of the spring-mass structure.
  • Weight can be saved on the part of heavy foil, which is an important requirement not only for electric vehicles. represents.
  • the temperature stability increases and the safety-relevant burning behavior is improved via the CNSL-based polyester diol or its ring structure.
  • Memory module 40 to 600 kl ⁇ l / m 2 60 to 90 100 to 600
  • Rokopol® Ml 170 (PCC Rokita), a copolymer of ethylene oxide and propylene oxide based on glycerol, was used as the cell opener.
  • Specflex® NS540 (DOW Chemicals) was used as MDI component, NCO content 31.36 to 32.57%, acidity 130 to 170mg / kg, viscosity 38 to 60mPa.s at 25 ° C.
  • RZETA® (Tosoh Corporation) is an amine-based, reactive gel catalyst that is derived from TEDA and is actively integrated in the PUR matrix via the OH group.
  • Dabco® NE300 (Evonik, formerly Air Products) supported the water-isocyanate reaction as a so-called blowing or blowing catalyst and was reactively integrated via the hydrogen-acidic NH group.
  • Tegostab® B8736LF2 is representative of the low-fogging silicone surfactants, which were mainly used for cell stabilization, also had an influence on cell size and distribution and improved the miscibility of the components used.
  • Concentrol® STB-PU1259PF is also an emission-optimized stabilizer from Productos Concentrol.
  • Embodiment for highly viscoelastic flexible molded foam in the sense of the present invention (quantity in parts by weight)
  • Example 2 Embodiment for viscoelastically modified flexible molded foam (improved damping behavior due to higher loss factor with the same density / avoidance - from an acoustic point of view undesirable increase in foam hardness) in the sense of the present invention

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne une formulation de mousse de polyuréthane à base de polyols polyéther et de polyols polyester conventionnels à base de matières premières renouvelables avec en particulier du MDI pour la fabrication de préférence de mousses moulées de PUR viscoélastiques et d'isolations acoustiques comportant des mousses à base de cette formulation.
EP19804674.0A 2018-11-28 2019-11-11 Formulation de mousse de polyuréthane et isolations acoustiques comportant des mousses à base de cette formulation Pending EP3887419A1 (fr)

Applications Claiming Priority (2)

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DE102018130176.6A DE102018130176A1 (de) 2018-11-28 2018-11-28 Polyurethan-Schaumstoff-Formulierung und Schallisolierungen mit darauf basierenden Schäumen
PCT/EP2019/080857 WO2020108971A1 (fr) 2018-11-28 2019-11-11 Formulation de mousse de polyuréthane et isolations acoustiques comportant des mousses à base de cette formulation

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EP3887419A1 true EP3887419A1 (fr) 2021-10-06

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US (1) US12043692B2 (fr)
EP (1) EP3887419A1 (fr)
JP (1) JP2022513146A (fr)
CN (1) CN113348190B (fr)
DE (1) DE102018130176A1 (fr)
WO (1) WO2020108971A1 (fr)

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DE102018130176A1 (de) 2018-11-28 2020-05-28 Adler Pelzer Holding Gmbh Polyurethan-Schaumstoff-Formulierung und Schallisolierungen mit darauf basierenden Schäumen

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US12043692B2 (en) 2024-07-23
WO2020108971A1 (fr) 2020-06-04
JP2022513146A (ja) 2022-02-07
DE102018130176A1 (de) 2020-05-28
CN113348190A (zh) 2021-09-03
CN113348190B (zh) 2023-11-17
US20220025099A1 (en) 2022-01-27

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